Chicago’s Westside Foodie Ride Bike Tour

  • 4 Hours12:00pm Fri-Sun
  • Ages from 21+
  • Easy/Moderate
  • Length: 12mi / 20km
  • VIP Alcohol Pairing Upgrade $19.99
  • Electric Bike Upgrade $29.99

Westside Foodie Bike Tour

Hop on a bike and discover a whole new side of Chicago dining in the westside! On this Chicago culinary tour, taste your way through diverse neighborhoods as we explore Chicago’s immigrant history through food. Enjoy the local eateries and unique foods that make Chicago such an amazing and delicious place to live. Tour Chicago’s westside by bike with restaurant pit stops along the way and a cultural experience you’ll remember!

All food and non-alcoholic beverage samples included in ticket price. Consider a VIP upgrade to include alcohol/beer pairings.

What’s Included

  • Tour prices include all food samples. *VIP Alcohol Pairing Upgrade at $19.99
  • Three craft beers with the VIP Alcohol Pairing Upgrade
  • Storied history of Chicago’s classic dishes and the establishments that created them
  • Informative bike tour of Chicago’s west side neighborhoods

What to Bring

  • Please bring an ID
  • Please bring a bottle of water. A few restaurants will serve water, but not all of them. So it’s highly recommended to bring a bottle of water.
  • Wear comfortable clothing/shoes

Important Info

  • Additional Costs might be incurred for restricted diets or changes to menu items.
  • Please arrive 15 minutes before scheduled tour time!
  • Tours run snow, rain, or shine!

Departure Locations

  • Bobby’s Bike Hike Headquarters (540 N. Lake Shore Drive)

What to Expect

On this popular Chicago food tour, you will embark upon an exciting bicycle adventure through the vibrant West Side neighborhoods of Chicago. Inspired by some of the Windy City’s most prominent immigrant communities and original recipes, this tour showcases a fresh perspective of our diverse town.

Bypass the wait at some of the city’s most popular restaurants and focus on enjoying amazing food and beverages! The best burgers on the planet, craft beer optional upgrade, Polish pierogi, gourmet barbecue sandwiches, Swedish liqueur (optional upgrade), and rich gourmet chocolate flavor this thirteen mile ride with authentic Chicago-style. Our enthusiastic local tour guides will lead you through an unforgettable afternoon of history and cuisine, sure to make memories that will last a lifetime.

The journey begins at the Bobby’s Bike Hike headquarters, where you’ll meet your fun-loving and safety-conscious tour guide.

From there, you’ll bike up to a beautiful view of The Chicago River, a critical component of the city’s growth and development. You’ll ride through our famous lower streets like they do in The Dark Knight films, and then roll by the upscale eateries and nightclubs of River North.

The first stop on the tour is the Fulton Market district, formerly home to meat packing and produce distribution companies. The area is now heavily sought-after real estate for tech giants, young startups, and trendy new restaurants.

Here you’ll feast on delicious Led Zeppelin sliders served with award-winning local craft beer. The brews vary with season, but always deliver on creativity and nuanced flavor.

From Fulton Market, the tour will ride into Ukrainian Village, home to a wide range of highly esteemed Eastern European eateries. You’ll taste three different Polish pierogi, guaranteed to satisfy any cravings for savory stuffed pastries.

Next up is Wicker Park, a well-known Chicago artists’ community. The food of this area is just as creative as the residents. While you’re here, you’ll enjoy a tasty, authentic taco that was recently ranked ’50 best tacos in America.’

Adjacent to Wicker Park is Bucktown, where you’ll enjoy a ride through amazing old homes mixed with modern mansions.

After that, you’ll head back over the river into Old Town, a historic Chicago neighborhood that began as an artists’ haven. You’ll experience one of Chicago’s finest chocolatiers, and sample their rich, decadent drinking chocolate before heading back downtown.

The final leg of your journey is a beautiful ride alongside Lake Michigan. Catch a glimpse of the beaches and the skyline that define this beautiful town, and be a part of the city’s vibrant bicycle culture while cruising the wide Lakefront Trail.

After thirteen miles and four hours, the tour wraps up back at Bobby’s headquarters in Streeterville.



Extra Information

The Chicago River is the only river in the world that flows away from its mouth, and the reason for Chicago’s entire history of trade and commerce.

For the first 100 years of Chicago’s history, Fulton Market was a center of meatpacking and produce distribution. Now the trendy neighborhood and its low-rise warehouse buildings is home to some of the Windy City’s most esteemed restaurants and corporate headquarters.

There are few things that Chicagoans love more than craft beer. Microbreweries and big name beer brands have found a home and a loyal audience here for generations.

In 2016, online real estate brokerage Redfin named Ukrainian Village “the hottest neighborhood in the country” due to booming real estate prices and boasts an abundance of restaurants serving Eastern European fare.

Wicker Park is Chicago’s most famous arts district, home to more bookstores, record shops, and coffee houses per capita than any other neighborhood in Chicago.

The 606 Trail is a converted elevated freight line that now serves as a winding 2.7-mile bike and walking path on Chicago’s west side.

Old Town is one of Chicago’s most historic North Side neighborhoods. Beloved by beatniks in the 1950s and 60s, and hippies in the 70s, Old Town is now a quiet, tree-line arts district.

Drinking chocolate, also known as “sipping chocolate,” is a rich treat made by melting small bits of fine chocolate and blending with milk or cream.

The Lakefront Trail has been connecting Chicago’s north and south side neighborhoods since 1963. It spans 18 miles of the beautiful Lake Michigan waterfront and has played a large role in connecting Chicago’s vibrant cycling community.


Bonci Pizza Esteemed pizzaiolo, Gabriele Bonci from Rome, creates pizzas that are so delicious, so creative, and so visually stunning that he has developed a fanatical following not only in Italy, but around the globe. Bonci is a reinvention of pizza that embraces quality above all else.  Enjoy a paired sangria with the VIP Alcohol Upgrade.

Kasia’s Deli has been a West Town institution since the 1980s and was chosen as one of Chicago’s favorite comfort foods by Chicago’s Best in 2017.

Recently awarded the title ’50 best Tacos in America’, Antique Taco is a combination of everything husband/wife owners Rick & Ashley Ortiz love: flavorful food, antique style, and the comfort of home.

Butcher and the Burger. We’ll stop by this popular Lincoln Park hangout to try their famous homemade custard, a popular midwestern dessert staple.  Choose between their delicous vanilla, chocolate, or their ‘flavor of the day.’

Cocoa & Co is a gourmet chocolate cafe and coffee bar in the Old Town neighborhood, with a heavy focus on sustainability and terroir.

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